2-(2-Fluoro­phen­yl)-5-iodo-7-methyl-3-methyl­sulfinyl-1-benzo­furan

Hong Dae Choi; Uk Lee

doi:10.1107/S1600536814010459

. 2014 May 17;70(Pt 6):o659. doi: 10.1107/S1600536814010459

2-(2-Fluorophenyl)-5-iodo-7-methyl-3-methylsulfinyl-1-benzofuran

Hong Dae Choi ^a, Uk Lee ^b,^*

PMCID: PMC4051089 PMID: 24940242

Abstract

In the title compound, C₁₆H₁₂FIO₂S, the dihedral angle between the plane of the benzofuran ring system (r.m.s. deviation = 0.023 Å) and that of the 2-fluorophenyl ring is 39.78 (7)°. In the crystal, molecules are linked via pairs of I⋯π contacts [3.812 (2) Å] and a π–π interaction between the benzene rings of neighbouring molecules [centroid–centroid distance = 3.821 (2) Å] into inversion dimers. These dimers are further linked by π–π interactions between the furan and benzene rings of neighbouring molecules [centroid–centroid distance = 3.668 (2) Å]. The molecules stack along the a-axis direction. In addition, C—H⋯O hydrogen bonds are observed between inversion-related dimers.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010 ▶, 2012 ▶, 2014 ▶).

Experimental

Crystal data

C₁₆H₁₂FIO₂S
M _r = 414.22
Monoclinic,
a = 7.9460 (2) Å
b = 24.1545 (7) Å
c = 7.9685 (2) Å
β = 100.997 (1)°
V = 1501.32 (7) Å³
Z = 4
Mo Kα radiation
μ = 2.28 mm⁻¹
T = 173 K
0.42 × 0.40 × 0.13 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.541, T _max = 0.746
14688 measured reflections
3721 independent reflections
3465 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.026
wR(F ²) = 0.059
S = 1.12
3721 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814010459/hb7228sup1.cif

e-70-0o659-sup1.cif^{(23.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814010459/hb7228Isup2.hkl

e-70-0o659-Isup2.hkl^{(182.4KB, hkl)}

Click here for additional data file.^{(5.4KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814010459/hb7228Isup3.cml

CCDC reference: 1001669

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2ⁱ	0.95	2.49	3.355 (3)	151
C15—H15⋯O2ⁱⁱ	0.95	2.48	3.185 (3)	131

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

This work was supported by Dong-eui University grant No. 2014AA013.

supplementary crystallographic information

1. Comment

As a part of our ongoing study of 5-iodo-7-methyl-3-methylsulfinyl-1-benzofuran derivatives containing 4-fluorophenyl (Choi et al., 2010), 3-fluorophenyl (Choi et al., 2012) and 4-methylphenyl (Choi et al., 2014) substituents in 2-position, we report here on the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.019 (2) Å from the least-squares plane defined by the nine constituent atoms. The 2-fluorophenyl ring is essentially planar, with a mean deviation of 0.012 (2) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the benzofuran ring system and the 2-fluorophenyl ring is 39.78 (7)°. In the crystal structure (Fig. 2), molecules are linked via pairs of C4–I1···π contacts between the iodine atom and the furan ring of a neighbouring molecule with a C4–I1···Cg1^iv = 3.812 (2) Å (Cg1 is the C1/C2/C7/O1/C8 furan ring), and by a π···π interaction between the benzene rings of neighbouring molecules, with a Cg2···Cg2^iv distance of 3.821 (2) Å and an interplanar distance of 3.581 (2) Å resulting in a slippage of 1.333 (2) Å (Cg2 is the C2-C7 benzene ring), into inversion dimers. These dimers are further linked by π···π interactions between the furan and benzene rings of neighbouring molecules, with a Cg1···Cg2ⁱⁱⁱ distance of 3.668 (2) Å and an interplanar distance of 3.375 (2) Å resulting in a slippage of 1.437 (2) Å. The molecules stack along the a-axis direction. In addition, C–H···O hydrogen bonds (Table 1) are observed between inversion-related dimers.

2. Experimental

3-Chloroperoxybenzoic acid (77%, 224 mg, 1.0 mmol) was added in small portions to a stirred solution of 2-(2-fluorophenyl)-5-iodo-7-methyl-3-methylsulfanyl-1-benzofuran (358 mg, 0.9 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 6h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane-ethyl acetate, 1:1 v/v) to afford the title compound as a colorless solid [yield 72%, m.p. 469-470 K; R_f = 0.48 (hexane-ethyl acetate, 1:1 v/v)]. Colourless blocks were prepared by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.